1470004-60-4Relevant academic research and scientific papers
Formal meta-specific intramolecular Friedel-Crafts allylic alkylation of phenols through a spirocyclization-dienone-phenol rearrangement cascade
Yoshida, Mariko,Nozaki, Tomoyuki,Nemoto, Tetsuhiro,Hamada, Yasumasa
, p. 9609 - 9615 (2013)
Formal meta-specific intramolecular Friedel-Crafts allylic alkylation of phenols was achieved based on spirocyclization-dienone-phenol rearrangement cascades. Systematic screening of acid catalysts revealed that Sc(OTf) 3 was a highly effective catalyst for dienone-phenol rearrangement of spiro[4.5]cyclohexadienones. Using 5 mol % of Sc(OTf)3 as the promoter, various spirocyclic substrates were transformed into the corresponding phenol derivatives in good to excellent yield. Furthermore, the one-pot sequential spirocyclization-dienone-phenol rearrangement proceeded using a palladium and scandium multi-catalytic system or a triphenylmethyl cation single-catalyst system, providing the corresponding meta-allylated phenol derivatives in excellent yield.
